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United States Patent | 5,194,380 |
Matsuyama ,   et al. | March 16, 1993 |
Optically active 2-hydroxy-4-phenyl-3-butenoic acid can be obtained by treating 2-oxo-4-phenyl-3-butenoic acid with an optionally treated microorganism capable of asymmetrically reducing the 2-oxo-4-phenyl-3-butenoic acid into (R)-2-hydroxy-4-phenyl-3-butenoic acid or (S)-2-hydroxy-4-phenyl-3-butenoic acid to thereby asymmetrically reduce the same into (R)-2-hydroxy-4-phenyl-3-butenoic acid or (S)-2-hydroxy-4-phenyl-3-butenoic acid.
Inventors: | Matsuyama; Akinobu (Niigata, JP); Takase; Ichiro (Hyogo, JP); Ueda; Yoichiro (Hyogo, JP); Kobayashi; Yoshinori (Niigata, JP) |
Assignee: | Daicel Chemical Industries, Ltd. (Sakai, JP) |
Appl. No.: | 459787 |
Filed: | March 1, 1990 |
PCT Filed: | July 11, 1989 |
PCT NO: | PCT/JP89/00698 |
371 Date: | March 1, 1990 |
102(e) Date: | March 1, 1990 |
PCT PUB.NO.: | WO90/00613 |
PCT PUB. Date: | January 25, 1990 |
Jul 12, 1988[JP] | 63-173469 | |
Jul 12, 1988[JP] | 63-173470 | |
Oct 07, 1988[JP] | 63-253020 |
Current U.S. Class: | 435/146; 435/280; 435/822; 435/827; 435/830; 435/836; 435/840; 435/843; 435/850; 435/852; 435/853; 435/857; 435/873; 435/874; 435/885; 435/911; 435/921; 435/930 |
Intern'l Class: | C12P 007/42; C12R 001/22; C12R 001/01; C12R 001/645 |
Field of Search: | 435/146,280,822,824,830,836,840,843,850,852,853,857,873,824,885,911,921,930 |
Foreign Patent Documents | |||
61-87640 | Oct., 1984 | JP. |
Biotech Abs 85-12678 (J60156394) Aug. 1985. Biotech Abs 90-05694 (J02016987) Jan. 1990. Biotech Abs 89-14981 (WO8907147) Aug. 1989. Biotech Abs 90-03378 (EP-347374) Dec. 1989. Nerdel et al. (1956) Chem. Ber., 89:671-677. |
TABLE 1 ______________________________________ Yield of Optical purity of (R)-2-hydroxy- (R)-2-hydroxy-4- 4-phenyl-3- phenyl-3-butenoic butenoic acid acid Strain (%) (% e.e.) ______________________________________ Lactobacillus lactis 11 67 AHU 1059 Streptococcus faecalis 14 62 IFO 12964 Leuconostoc mesenteroides 92 100 subsp. dextranicum IFO 3349 Pediococcus acidilactici 10 100 NRIC 1102 Sporolactobacillus 16 68 inulinus NRIC 1133 Lactobacillus lactis 16 100 ATCC 12315 Lactobacillus 14 46 Viridescens ATCC 12706 Leuconostoc dextranicum 96 100 ATCC 17072 Leuconostoc mesenteroides 93 100 AHU 1067 Arthrobacter citreus 20 100 IAM 12341 Agrobacterium radiobacter 13 100 IFO 12664 Ambrosiozyma cicatricosa 11 100 IFO 1846 Ambrosiozyma 10 100 platypodis IFO 1471 Achromobacter pestifer 15 100 ATCC 23584 Arthroascus javanensis 12 32 IFO 1848 Aureobacterium testaceum 12 20 IFO 12675 Bacillus licheniformis 10 100 IFO 12200 Botryoascus synnaedendrus 13 100 IFO 1604 Brevibacterium iodinum 15 100 IFO 3558 Candida parapsilosis 19 100 IFO 1396 Saccharomycopsis lipolytica 12 100 IFO 1550 Saccharomycopsis fibuligera 13 100 IFO 0103 schizosaccharomyces 10 100 octosporus IFO 0353 Stephanoascus ciferrii 19 100 IFO 1854 Torulaspora delbrueckii 14 100 IFO 0381 Trigonopsis variabillis 15 100 IFO 0755 Wickerhamiella domercquii 11 95 IFO 1857 Enterobacter aerogenes 13 94 AHU 1338 Klebsiella pneumoniae 12 70 IAM 1063 Xanthomonas oryzae AIM 11 100 1657 Lactobacillus plantrum 24 99 IFO 3070 Streptococcus lactis 32 49 NRIC 1149 Leuconostoc mesenteroides 14 100 AHU 1416 Candida rugosa IFO 0750 17 100 Clavispora lusitaniae 16 100 IFO 1019 Corynebacterium 11 93 glutamicum ATCC 13032 Flavobacterium suaveolens 11 70 IFO 3752 Geotrichum candidum 19 100 IFO 4601 Hansenula facianii IFO 1253 13 100 Kluyveromyces lactis 14 100 IFO 1903 Lipomyces starkeyi IFO 10 83 1289 Lodderomyces elongisporus 14 100 IFO 1676 Proteus vulgaris IFO 3167 10 100 Pseudomonas aureotaciens 11 100 IFO 3522 ______________________________________